From Karrueche to Rihanna: Chris Brown’s Dating History Hits Different

The Breakdown: Few singers have had a career and dating history as poppin’ as Chris Brown’s. The singer has been involved in several high-profile relationships and is now a father of three.

In addition to his booming career, Chris Brown’s dating history has been a rollercoaster. The singer’s romantic life has been filled with high-profile romances, baby mama drama, and a few situationships. Here's a rundown of Breezy's most talked-about relationships.

Chris and Rihanna were the ultimate power couple until their relationship took a turn. The two met as teenagers in 2004 and began dating in 2008. In February 2009, Chris assaulted Rihanna, leading to his arrest and a felony assault charge. He later pleaded guilty and was sentenced to five years of probation and community service.​ Despite the assault, the pair rekindled their relationship in 2012, collaborating on remixes of Rihanna's "Birthday Cake" and Brown's "Turn Up the Music."

Karrueche Tran had an on-and-off relationship with Chris starting in 2011. Their romance was riddled with infidelity rumors and drama, including an alleged love triangle with Rihanna. Chris briefly rekindled his relationship with the “Love on the Brain” singer in 2012, leading to a temporary split with Karrueche. Chris and Karrueche reconciled later that year, but the on-and-off nature of their relationship continued. In 2015, Karrueche ended the relationship after discovering that Chris had fathered a child with another woman.

In February 2017, Karrueche filed for a restraining order against Chris, accusing him of physical abuse during their relationship and threatening her life after the breakup. She told the court that Chris punched her in the stomach twice and pushed her down the stairs years earlier. She also submitted text messages and voicemails in which Chris demanded the return of gifts and issued violent threats. In June 2017, a judge granted Karrueche a five-year restraining order against him.

Chris and Nia Guzman had a brief affair while he was dating Karrueche. In 2014, news broke that Chris had a child with Nia, leaving Karrueche shocked. Nia later revealed that Brown was aware of Royalty's existence before the public knew. "He always knew about her; he just wasn’t ready to deal with the situation,” Nia said (per Essence). “But it’s been quite the experience. I can’t say anything positive about it … at all. Nothing positive.”

Their co-parenting battle was just as messy, with Nia requesting full custody of their daughter, Royalty. However, in 2016, a judge denied her requests, granting Chris joint custody and unsupervised visitation rights. Despite past drama, Chris and Nia have seemingly made strides in co-parenting. They've been seen together at their daughter's events, supporting Royalty together.

Whispers about Chris’ relationship with Ammika Harris began in 2015. After a period apart, they got back together in 2019, leading to the birth of their son, Aeko Catori, in November of that year, according to People. Chris and Ammika have maintained a strong co-parenting relationship.

Chris Brown and Diamond Brown's relationship has been a topic of conversation since they first linked in 2019. Chris and Diamond kept a low profile, she supported him on tour, but their time together seemed casual. Things eventually got serious, leading to the birth of their daughter, Lovely Symphani Brown, in January 2022.